Serena and Chuck, A love story
by xxrubyprincessxx
Summary: A Serena and Chuck romance story. I have changed a lot of the characters backgrounds, please give me feedback thanks!
1. Chapter 1

Jennifer Humphrey is one of the most sought-after girls at school this month, however one year from today she was practically irrelevant. You see, since her arrival to the Desmond Knight School, Jenny had always been considered a wannabe; her weight problem didn't help her image any either. It's thanks to my best friend Blair Waldorf and indirectly myself that her whole life changed for the better. I don't know Jenny very well but Blair has always been great at seeing the potential in people that others tend to overlook, so when she decided to take Jenny on as a project I supported her 110%. Blair and I attend the Florence Cooper Academy, while Jenny, as I stated earlier, goes to Desmond Knight just down the street. Tonight Blair and I decided to attend Jenny's New Years party over on Upper West for two reasons: one, because we had nothing better to do, and, two, my crush since freshman year, Nate Archibald, was going to be there.

I arrived at Blair's around 8:00; she lives by herself in a beautiful brownstone that her father bought her last year. Mr. Waldorf is a real estate tycoon who at one time owned about half of Manhattan. Since he is always away on business anyway, Mr. Waldorf thought it would be a good idea for Blair to have a place of her own. Mrs. Waldorf died when Blair was only five; she committed suicide by jumping from the 12th floor of the family's townhouse in Paris. Both of my parents are alive and well, but like Blair I rarely see ether of them. My father inherited his fortune from my grandfather, Henry Van Der Woodsen, the Media Mogul. His current net worth is in the 7.5 billion range, making daddy one of the richest men in Manhattan. My mother's family is what you would call old money; she is a direct heiress to the Graham Steel fortune. My parents are still married, on paper that is, but its no secret they have been emotionally divorced for years now. My father is currently dating a Brazilian supermodel, and my mother has been spotted on various occasions with her personal trainer "after hours". Growing up was a lonely time for me, as I was practically raised by nannies and had no siblings. That's why my friendship with Blair is so important to me, as she really became a sister to me and I feel like I connect with her on a deeper level. Most kids don't really understand what its like to have the lives Blair and I do; she is one of the few people I can be completely "real" with. After briefly catching up, Blair and I got ready for the party. I was wearing a black Dior Cocktail dress, black Yves Saint Laurent pumps, and a patent leather clutch by Hermès. Blair had on a purple Christian Lacroix baby doll dress, black Chanel jacket, black stilettos and navy purse both by Prada.

"So are you going to hook up with Nate tonight?" Blair asked.

"Blair! Really?"

"What!? Serena, you have been crushing on him since what, 9th grade? Just ask him out already!"

"Okay, who said anything about wanting to ask him out? He's a nice guy, but just a friend."

"Oh don't even give me that Serena, you LOVE him!" she said half-heartedly.

"Please… I mean he could have any girl he wanted…"

"But you are not 'any girl', you're Serena Van Der Woodsen! Guys want you and girls want to be you!"

"Look Blair, really I don't know what I want right now and I know Nate is really the only reason either of us is going to this party but I am having second thoughts…could we just not mention him for the rest of the night?"

"Serena! Come on…"

"Blair please! I just don't want to think about him or love or boys right now, okay?"

"I understand. No problem, there will be no Nate talk until you tell me otherwise."

"Thanks Blair, I appreciate it."

"Damn! Serena its almost 9:30, we gotta get going! I'll call the driver."

The first thing I noticed as I entered Jenny's penthouse was how tacky her party decorations looked with the interior design of her living room, however my attention was quickly drawn to a boy sitting alone on the other side of the room.

"Blair, who is that boy over there?"

"Who? In the green blazer? God that's Tomm…"

"Nooo, next to him, in the blue."

"Oh, that's Chuck Bass! Come let me introduce you."

But before we had even made two steps past the entryway, Jenny had spotted us, "If it isn't Blair Waldorf and Serena Van Der Woodsen! I am so glad you two made it!" Jenny was wearing a bright pink ruffled slip dress by Versace, pink ballet heels by John Paul Gaultier and a matching diamond bracelet, necklace and earrings all by Van Cleef & Arpels.

"We were getting worried! I mean I've heard of fashionably late, but two hours is pushing it even for you two!" I knew she was kidding but I could tell by her tone she was annoyed

"Don't blame Blair, it was all my fault… you know how long it takes me to get ready, I'm sorry love."

"Oh you know I'm kidding Serena, Come now I have some people to introduce you to!" I quickly shot Blair a look of disapproval and she jumped in

"Um…Actually Jenny… Serena and I were going to, uh, freshen up, but we will be right back, alright?"

"Oh… okay...that's fine, I'll be out here…" We rushed off before she could finish.

"That was close. I don't know how you put up with that on a daily basis Blair."

"As if! Jenny is a project, not a best friend. If I didn't know any better I would think you were jealous…" Before I could even come up with a comeback someone came barreling past me, almost knocking me over.

"Excuse me! Could you please watch where…" And than I saw him, the boy in blue: Chuck Bass.

"Oh, I apologize, I guess I should call it a night, huh?" he said, glancing at his half finished martini. Caught off guard I foolishly replied, "Um, no, its my fault, I mean its fine, I'm fine… I'm sorry…"

"I was kidding," he laughed.

"Chuck, this is Serena Van Der Woodsen, Serena…"

"Chuck Bass," he interrupted before Blair could even finish.

"Well, I'll let you two get better acquainted. I will be helping Jenny keep what's left of this party from dying if anyone needs me," Blair said in a half joking manner as she left us alone.

Chuck was just about 6ft tall with wavy brown hair, thick eyebrows and the most beautiful brown eyes I had ever seen. He was wearing a navy blue button up by Burberry Prorsum, black Philipp Plein jeans, black Armani vest and patent leather Dior Homme lace ups. "So I finally get to meet the infamous Serena Van Der Woodsen."

"Infamous huh?"

"Of course, you know you're somewhat of a celebrity at Woodcrest. Let's just say you make a lot of girls pretty jealous."

"I can't imagine why…"

"I can, you certainly live up to the expectations, I mean look at you!"

By this point, knowing my face must have turned a bright shade of red, I feebly tried to change the subject. "So you go to Woodcrest? Do you know Nate? Nate Archibald? He attends Woodcrest as well."

"Wasn't he just here? Did you two date or something?" he asked.

"No! We're just friends… I mean used to be… I haven't seen him for a while, that's all." "Well to be honest, Serena, this is my first year at Woodcrest. It's basically the last decent school that would take me since I got kicked out of boarding school."

I don't know why, but after hearing that, I wanted him even more than before, but I attempted to keep my cool and appear as uninterested as I could.

"Oh, is that so… So what, are you suppose to be a rebel or something…"

At that, he just smiled, and something inside of me said turn away and never look back but I was frozen, as if he had a hold on me. Then, he leaned in to kiss me and I wanted nothing more at that moment, but I got myself together just in time "No, not here." I said. I was not about to end up on the prep gossip blogs for making out with a total stranger at a party, that was not my style. I Serena Van Der Woodsen, held myself to a higher standard. However, what people didn't know couldn't hurt me.

"Lets go somewhere more private… the guest bedroom."

That was all Chuck needed to hear, before I knew it he was whisking me down the hallway, however just as we passed the corner I locked eyes with none other than Sharpay Evans. My heart froze. Sharpay, aside from being the class bitch, had a penchant for spreading gossip. After about 5 seconds of contemplation, however, the distraction of Chuck took over and Sharpay was out of my mind just as fast as she had entered it. As soon as we had entered the guest bedroom on the second floor of Jenny's penthous Shane threw me onto the bed, the blue-stripped Missoni comforter felt like heaven against by back, and before I knew it, Chuck was on top of me and the two of us were ferociously making out. For a moment I forgot about all of my problems, all the drama just disappeared, I wanted that moment forever. Caught up in my lust, I thought to myself, 'I want Chuck Bass forever.' I felt Chuck's hands all over my body as he was trying to unzip the back of my Dior dress. I was about to fully give in to my desire when suddenly a hard knock on the door caused my heart freeze. "Serena? Is that you in there?"; I knew that voice immediately, it was…Nate! Nate Archibald, my sick obsession for over a year was at the door. If he saw me like this, with Chuck! My heart pounded as I heard the antique brass bedroom door handle turn, having no idea what was in store for me next.


	2. Chapter 2

AN: I got a few comments on my first chapter so I decided to continue the story, If you enjoy it please let me know and leave a comment it motivates me. I am also open to suggestions on including characters, even non GG characters. Thanks for the support everyone!

It took me all but two seconds to push Chuck off myself, I know it was terribly rude but I panicked at the thought of completely ruining any chance I had with Nate. I mean Chuck Bass was incredibly sexy but this was Nate Archibald, we had history. Just as a sliver of light from the hallway begins to hit my face I yell, "Don't come in! I'm, um, changing!" and with that the door was slams shut once again, a sigh of relief washes over me like a cool wave, I am saved… for now.

"Now what did you do that for!" Chuck asks, clearly annoyed.

"Be quiet! Please!"

"What's going on Serena?"

"Look, I can't have anyone knowing we're together in here, they could get the wrong idea."

"Wrong idea? Are you kidding me!"

Than comes another knock, "Are you alright in there?" asks the voice on the other side, I cannot believe it, the voice is Nate Archibald.

"Oh yes! Um, I'm fine… could you just give me a minute please, I will be right out."

"This is ridiculous, I'm leaving." barks Chuck.

"No please! Look Chuck I'm sorry, its not you. Please, could you just wait?"

"So what was this than?"

"What?"

"This, us, this whole make out session? I thought you were into me. It's that Nate guy, that's whose out there isn't it"

"Yes, he's the one who knocked but…"

"Do you like him?"

"What? No, he's…"

"Seriously Serena, he's clearly not 'just a friend', you wouldn't be freaking out like this if he was"

"Look Chuck, I'm sorry, I do like you, I wouldn't have come to this room with you if I didn't, but… I have history with Nate, I don't know how to explain it right now."

"I understand…" he says, from the tone of voice I can tell he is hurt.

"Chuck…"

"You want the truth Serena, I only came to this party in the hope of seeing you."

"What?"

"I have had a crush on you since I first saw you, two months ago, Elena Gilbert's party. I was too afraid to introduce myself, you were just so stunning in that white Lacroix dress"

I am shocked, both flattered and taken aback at the same time, I am not even sure how to react to such an intimate confession.

"Chuck, I had no idea…"

"Well now you do. I was about to leave tonight, until I bumped into you, I swear I thought it was fate or something." he laughs.

"I really do like you Chuck, I have since I first saw you tonight, sitting alone across the room. I just… I don't know what I want, I'm not even sure what I should say right now…"

"Don't say anything Serena, I understand… Don't worry, I wont ruin things for you and… Nate. It was nice while it lasted, have a good night Miss. Van der woodsen…" I can feel the melancholy in his voice and my heart breaks for him, after that he slowly openes the door a crack to be sure the coast is clear before slipping away.

"Chuck, wait…" I call out quietly, but it is too late, he's gone.

As I head back downstairs I spot Nate by the wet bar conversing with Zoey Brooks and, to my dismay, Sharpay Evens. Nate is wearing a light grey Ralph Lauren blazer, white Hugo Boss dress shirt, black Dior Homme jeans and a pair of Alden wingtips. Zoey has on a white Dolce and Gabanna fringe dress, white Sergio Rossi heels, a silver Tiffany charm necklace and matching bracelet; Sharpay is in a slutty zebra print gown by Caserenali, metal-studded Rick Owen pumps, and Austrian crystal earrings by José and Maria Barrera.

"Hey Serena! There you are, sorry for almost walking in on you earlier, Sharpay told me you were upstairs I didn't realize you were changing." Nate says, and judging by the look on his face I can tell he is genuinely excited to see me.

"Oh yes, I spilled a drink on my dress earlier…"

"It looks fine to me." says Sharpay while shooting me a dirty glance.

"Wonderful, I was so scared it was going to stain." I reply in a condescending tone.

Sharpay and I have been "frenimies" since as long as I have had the displeasure of knowing her, but wile I absolutely despise the girl we run in the same circles and so I am forced to act cordial around her in public. Sharpay however has made it her life's mission to destroy my reputation at any cost. I honestly don't know why she hates me so but Blair's theory is that Sharpay is just insanely jealous of me.

"Well anyhow, its great to see you Serena, its been a while" Nate says, almost making me blush with excitement.

"I agree, far too long!" Zoey chimes in, "Please, fill me in, what's the gossip at Florence Cooper? Is it true Veronica Mars and Scott McCall are together now?" She asks in a slurred voice, intoxicated as usual, Xanax most likely.

"Oh don't bother her with your nonsense Zoey, who cares about… Veronica McCall; lets hear about you Serena… seeing anyone these days?"

"Believe it or not Sharpay but I am still happily single" I steal a quick glace at Nate but cant tell if that news excites him in any way.

"That's the spirit, but I really hope you're not letting your breakup with Damon Salvatore sour you on dating all together, you're much to pretty for that." I could slap her for bringing up Damon but I am not about to give Sharpay the satisfaction of embarrassing me in front of everyone, including Nate, so I refrain and give her a faux half smile instead.

"I appreciate your concern Sharpay, but as you are well aware my breakup with Damon was over a year ago, I think its safe to say I have moved on"

"Well speaking of relations, I wouldn't mind getting together with that handsome Chuck Bass." Exclaims Zoey in a devious manner.

"Chuck who?" Sharpay mutters.

"I think he goes to Woodcrest with us, the new kid." Nate replies.

"Yes, you know Sharpay, he was in the blue, beautiful brown eyes." Zoey exclaims.

"Oh yes, of course. In fact I believe he and Serena were talking earlier."

"That is correct Sharpay, Blair introduced us after he nearly ran me over earlier."

"Oh is that so…" Sharpay smirks.

Knowing exactly where this conversation is headed I look for a way out, any way out. Noticing Zoey is barely conscious at this point I take my opportunity, "Zoey doesn't look so good, maybe you should get her a diet coke or something before she passes out."

"What am I, her mother? She's fine, don't worry about her"

"No, I think Serena's right Sharpay, Zoey looks pretty out of it, besides didn't she arrive with you?" Nate asks, almost sounding truly concerned.

"Look I said she was fi…" Before Sharpay is able to even finish her sentence Zoey stumbles backwards spilling her champagne all over Alex Russo. "Oh my god! My dress!" She screams. Alex is wearing a gold Strapless tube dress by Alexander McQueen, Black lace Manolo Blahnik pumps and a black Cartier wristwatch. At this point to save herself from further embarrassment Sharpay Evens reluctantly drags Zoey across the living room towards the washroom.

"Wow, now what was that! A party is never complete without Sharpay Evens and her marry band of burnouts I guess" Nate laughes as he watches them stumble off.

Realizing that Nate doesn't care much for Sharpay makes that whole ordeal worthwhile. "You wanna get out of here?" he asks. Trying to mask my immense excitement I reply. "Um, sure… You have some place in mind?"

"It's a surprise, you'll just have to trust me"

"Alright" I smile, "Let me just say goodbye to Blair, I'll meet you in the Lobby?"

"No problem" he replies.

I could die, my biggest high school crush Nate Archibald has just asked me if I wanted to go off alone with him, this is my chance. I rush over to Blair, who I spot near the black leather Barcelona couch,

"Blair, you wont believe what just happened! Nate asked me if I wanted to 'get out of here'!"

"Oh my god Serena! Are you serious?"

"Yes, I could die right now!"

"Well what are you doing here, go!"

"I just had to tell you, ill call you tonight okay."

"Yes, I want all the details, but get going before he changes his mind!"

"I will, I will, tell Jenny I had to… uh, make up an excuse for me, anything, and tell her I'm very sorry, bye!"

And with that I am off, I meet up with Nate in the lobby and he has the valet bring around his black Mercedes.

"New car?" I ask.

"Yeah, I bought it last week, what do you think?"

"I like it."

"Just wait till you get inside" he says slyly.

The streets look like a beautiful blur of colored lights as we zoom past Soho and into the meatpacking district.

"Where are we going?"

"It's a surprise"

Than he pulls over, we are at the docks, it looks so beautiful at night, the light from the full moon is glistening on the water as it quietly Lapps against the dock.

"Wow I never realized how beautiful this place was"

"Yeah, its really something isn't it. I used to come here when I needed to be alone. You know, to think. It's my secret spot… well I guess now it's our secret spot."

"Thank you Nate"

"For what?"

"Sharing this with me"

"Well you know Serena… well… I'm glad I ran into you tonight"

"Me too Nate"

"You mean a lot to me Serena, I don't think I've ever told you that. You've been a real great friend to me"

"Oh Nate…"

"What is it?" he asks with concern in his voice.

"…Nothing, its nothing" I reply shyly.

"This is so much harder than I thought it would be… Serena…"

"Yes Nate?"

"Have you ever thought about, well, what it would be like…"

"Nate, you can ask me anything, you know that."

"Serena… fuck it" And with that he leans in and kisses me, I admit I am genuinely caught off guard but I go with it and before I know it me and Nate Archibald are making out in the front seat of his Mercedes under bright purple moonlit sky.

By the time I get back to my penthouse it is already 3:30 in the morning, exhausted I pour myself a glass of Ty Nant and than quickly change into my cashmere Loro Piana nightgown before falling into bed with the sweet taste of Nate's lips still lingering on mine. My spirits are higher than they have been in a very long time, I am so full of excitement I can barely get myself to sleep, but as I close my eyes and began to drift off to sleep, one image keeps working its way back into my mind… Chuck Bass.


	3. Chapter 3

The Morning After

I woke up this morning with a small headache; I take two five-milligram Valiums, washing them down with a small swig of Ty Nant that I drink directly from the bottle. I glance at the gold Cartier Calibre that is resting on my nightstand and realized it is almost 4:00pm, I have severely overslept but considering the previous night it's not very surprising. Before I have a chance to even get out of bed my phone rings, its Nate.

"Hello Serena it's Nate, Nate Achibald. I just wanted to see… is this a bad time?" He asks with an overtly nervous tone in his voice.

"Nate, no, of course not, how are you?" I say tiredly.

"I am fine thank you, actually I wanted to see if you would like to have dinner with me tonight. I was thinking 7:00?"

"I would love to, where were you thinking?"

"How does Philippe Chow sound?"

"Trendy." I chortle.

"Great, sounds great, should I pick you up?" He asks.

I think for a moment and than realize that if I say yes he will probably pick me up around 6:30 and there is no way in hell I am going to be ready by than.

"No… I actually have some shopping to do today so I'll just meet you there at 7:00."

"Wonderful, see you than."

As I hang up I realize after last night I really should be more excited about our dinner date but for some reason my mind is somewhere else, something is distracting me, something I cant quite seem to put my finger on.

Philippe Chow

I arrive home around 6:00pm after a two hour shopping excursion at Barneys where I picked up a few dresses, two Valentionos, a Alexander McQueen and a Emilio Pucci. I also bought a Gucci saddle bag and a sterling silver Ralph Lauren jewelry box. I grab a diet Coke from the kitchen and then begin getting ready; After showering I put on a lavender backless dress by John Galliano, white six inch leather Louboutin heels, a diamond tennis necklace with matching diamond earrings by Harry Winston and about five silver diamond studded Cartier bangles on my wrist. I have my chauffeur pick me up in front of the apartment at 7:10 and I text Blair on the ride over to see what her plans are for tonight. Apparently she is having dinner with Scott McCall at Le Cirque and then most likely going to Marquee afterward. I tell her about my date with Nate and mention we should meet up at the club after dinner.

I finally arrive at Philippe Chow around 8:00 to meet Nate, as I walk upstairs I see him sitting in a large booth with two other people; his old friend Derek Hale and to my dismay Justin Russo. Justin associates with the likes of Georgina Sparks, Jenna Marshall and my crazy ex boyfriend Damon Salvatore therefore I tend to avoid him all together. Justin is actually quite handsome in a coked out bad boy sort of way but I have it on good authority that he is also quite the psychopath. In fact two years ago he was accused of raping Vicki Donovan but his father Jerry Russo just so happens to be the governor of New York so the charges were dropped and the case was "settled" out of court. Between his family's large fortune and his fathers vast political connections Justin could probably get away with murder if he really wanted to. It takes about two seconds for him to notice me walking up to their table.

"Well look who we have here, Serena darling it's been far too long…"

"Hello Justin." I reply coldly. He is wearing a charcoal Thom Brown tweed blazer, a black Brioni cashmere V-neck sweater and a maroon silk scarf by, I believe, Brunello Cucinelli. I quickly take my seat next to Nate who gives me a friendly kiss on my cheek, as he leans in I can smell the Tom Ford tobacco vanille he is wearing, it happens to be one of my favorite colognes.

"Glad you could make it." He whispers, trying to conceal a smile.

"But of course darling. I didn't realize this was going to be a party." I whisper back dejectedly.

Nate has on a taupe wool Valentino blazer, a navy button up by Paul Smith and black Dior Homme jeans. While Derek is wearing a Black Prada blazer, white pinstripe Emporio Armani shirt and a green silk bowtie by Hermès. Nate gives me a look of guilt but doesn't say anything.

"How are you tonight Serena, it's been a while." Derek exclaims.

"It certainly has, and I am quite well thank you"

"Well that is great news Serena." Justin responds sarcastically.

I shoot him a dirty look. "Surprised to see you at all Justin, in fact I didn't know you and Nate were acquaintances…"

"Actually we met at his sisters birthday party a few months back, you know Alex Russo right, weren't you there?" Nate enquiries.

"I must have missed that one." I reply.

"Well speaking of birthdays, mine is this weekend, will you be coming out with us Serena?" Justin asks.

"Oh you mean I'm invited? What an honor." I reply in a sarcastic tone.

"Well of course love. I rented out 1-Oak, and maybe afterwards we can go slumming in Brooklyn, what do you say?"

"Sounds like a blast… but I will have to check my schedule. I'll get back to you."

"Sounds good babe." Justin responds drolly.

I give him a faux smile and ask, "So what are you boys up to tonight? I mean, besides a lot of coke…"

"Oh Serena, you haven't lost that edge I see." Justin laughs.

Derek chimes in "We're going to a party, Lydia Martin rented a suite at the Four Seasons."

"In fact, I think we should be on our way Derek… would you two like to join us"

I give a Nate a glance of disapproval.

"No, I think we will stay." Nate responds.

"Whatever, Ill call you tomorrow Nate. Have a good night Serena…"

"You too Justin. You too."

As soon as Justin and Derek leave I sigh and turn to Nate. "Must you socialize with him, he's insufferable…"

"I'm sorry babe, he came with Derek."

"Well next time you invite me out for drinks you may want to mention the fact Derek and others may also be joining, I was under the impression it would be just the two of us."

"I apologize Serena, it was last minute, I couldn't get rid of them."

"Oh it's quite alright, lets just enjoy the rest of the night." I sigh.

"Sounds good to me, now what would you like to do tonight?"

"Well Blair has a table at Marquee if you're interested?"

"Sure, why not."


End file.
